{"id":"https://openalex.org/W2332356554","doi":"https://doi.org/10.1021/ol500389t","title":"A Photoinduced, Benzyne Click Reaction","display_name":"A Photoinduced, Benzyne Click Reaction","publication_year":2014,"publication_date":"2014-03-13","ids":{"openalex":"https://openalex.org/W2332356554","doi":"https://doi.org/10.1021/ol500389t","mag":"2332356554","pmid":"https://pubmed.ncbi.nlm.nih.gov/24625300"},"language":"en","primary_location":{"id":"doi:10.1021/ol500389t","doi":"https://doi.org/10.1021/ol500389t","is_oa":false,"landing_page_url":"https://doi.org/10.1021/ol500389t","pdf_url":null,"source":{"id":"https://openalex.org/S201989124","display_name":"Organic Letters","issn_l":"1523-7052","issn":["1523-7052","1523-7060"],"is_oa":false,"is_in_doaj":false,"is_core":true,"listed_in":["cwts-core","dongbi-a","jufo-2","ki-jl-2","medline","norway-2","poland-140","russia-white-list-1","vabb-shw"],"host_organization":"https://openalex.org/P4310320006","host_organization_name":"American Chemical Society","host_organization_lineage":["https://openalex.org/P4310320006"],"host_organization_lineage_names":["American Chemical Society"],"type":"journal"},"license":null,"license_id":null,"version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"Organic Letters","raw_type":"journal-article"},"volume":null,"type":"article","indexed_in":["crossref","pubmed"],"open_access":{"is_oa":false,"oa_status":"closed","oa_url":null,"any_repository_has_fulltext":false},"authorships":[{"author_position":"first","author":{"id":"https://openalex.org/A5037008192","display_name":"Adam W. Gann","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I24603500","display_name":"University of Massachusetts Amherst","ror":"https://ror.org/0072zz521","country_code":"US","type":"education","lineage":["https://openalex.org/I24603500"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Adam W. Gann","raw_affiliation_strings":["Department of Chemistry, University of Massachusetts, 710 North\rPleasant Street, Amherst, Massachusetts 01003, United States"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Chemistry, University of Massachusetts, 710 North\rPleasant Street, Amherst, Massachusetts 01003, United States","institution_ids":["https://openalex.org/I24603500"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5018308068","display_name":"Jon W. Amoroso","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I24603500","display_name":"University of Massachusetts Amherst","ror":"https://ror.org/0072zz521","country_code":"US","type":"education","lineage":["https://openalex.org/I24603500"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Jon W. Amoroso","raw_affiliation_strings":["Department of Chemistry, University of Massachusetts, 710 North\rPleasant Street, Amherst, Massachusetts 01003, United States"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Chemistry, University of Massachusetts, 710 North\rPleasant Street, Amherst, Massachusetts 01003, United States","institution_ids":["https://openalex.org/I24603500"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5003086858","display_name":"Vincent J. Einck","orcid":"https://orcid.org/0000-0001-5210-4395","observed_orcids":["https://orcid.org/0000-0001-5210-4395"]},"institutions":[{"id":"https://openalex.org/I24603500","display_name":"University of Massachusetts Amherst","ror":"https://ror.org/0072zz521","country_code":"US","type":"education","lineage":["https://openalex.org/I24603500"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Vincent J. Einck","raw_affiliation_strings":["Department of Chemistry, University of Massachusetts, 710 North\rPleasant Street, Amherst, Massachusetts 01003, United States"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Chemistry, University of Massachusetts, 710 North\rPleasant Street, Amherst, Massachusetts 01003, United States","institution_ids":["https://openalex.org/I24603500"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5067634758","display_name":"Walter P. Rice","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I24603500","display_name":"University of Massachusetts Amherst","ror":"https://ror.org/0072zz521","country_code":"US","type":"education","lineage":["https://openalex.org/I24603500"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Walter P. Rice","raw_affiliation_strings":["Department of Chemistry, University of Massachusetts, 710 North\rPleasant Street, Amherst, Massachusetts 01003, United States"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Chemistry, University of Massachusetts, 710 North\rPleasant Street, Amherst, Massachusetts 01003, United States","institution_ids":["https://openalex.org/I24603500"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5046591359","display_name":"James J. Chambers","orcid":"https://orcid.org/0000-0003-3883-8215","observed_orcids":["https://orcid.org/0000-0003-3883-8215"]},"institutions":[{"id":"https://openalex.org/I24603500","display_name":"University of Massachusetts Amherst","ror":"https://ror.org/0072zz521","country_code":"US","type":"education","lineage":["https://openalex.org/I24603500"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"James J. Chambers","raw_affiliation_strings":["Department of Chemistry, University of Massachusetts, 710 North\rPleasant Street, Amherst, Massachusetts 01003, United States"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Chemistry, University of Massachusetts, 710 North\rPleasant Street, Amherst, Massachusetts 01003, United States","institution_ids":["https://openalex.org/I24603500"]}]},{"author_position":"last","author":{"id":"https://openalex.org/A5066862270","display_name":"Nathan A. Schnarr","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I24603500","display_name":"University of Massachusetts Amherst","ror":"https://ror.org/0072zz521","country_code":"US","type":"education","lineage":["https://openalex.org/I24603500"]}],"countries":["US"],"is_corresponding":true,"raw_author_name":"Nathan A. Schnarr","raw_affiliation_strings":["Department of Chemistry, University of Massachusetts, 710 North\rPleasant Street, Amherst, Massachusetts 01003, United States"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Chemistry, University of Massachusetts, 710 North\rPleasant Street, Amherst, Massachusetts 01003, United States","institution_ids":["https://openalex.org/I24603500"]}]}],"institutions":[],"countries_distinct_count":1,"institutions_distinct_count":1,"corresponding_author_ids":["https://openalex.org/A5066862270"],"corresponding_institution_ids":["https://openalex.org/I24603500"],"apc_list":{"value":4500,"currency":"USD","value_usd":4500},"apc_paid":null,"fwci":2.6421,"has_fulltext":false,"cited_by_count":62,"citation_normalized_percentile":{"value":0.89579933,"is_in_top_1_percent":false,"is_in_top_10_percent":false},"cited_by_percentile_year":{"min":89,"max":99},"biblio":{"volume":"16","issue":"7","first_page":"2003","last_page":"2005"},"is_retracted":false,"is_paratext":false,"is_xpac":false,"primary_topic":{"id":"https://openalex.org/T12653","display_name":"Cyclization and Aryne Chemistry","score":0.8208000063896179,"subfield":{"id":"https://openalex.org/subfields/1605","display_name":"Organic Chemistry"},"field":{"id":"https://openalex.org/fields/16","display_name":"Chemistry"},"domain":{"id":"https://openalex.org/domains/3","display_name":"Physical Sciences"}},"topics":[{"id":"https://openalex.org/T12653","display_name":"Cyclization and Aryne Chemistry","score":0.8208000063896179,"subfield":{"id":"https://openalex.org/subfields/1605","display_name":"Organic Chemistry"},"field":{"id":"https://openalex.org/fields/16","display_name":"Chemistry"},"domain":{"id":"https://openalex.org/domains/3","display_name":"Physical Sciences"}},{"id":"https://openalex.org/T11440","display_name":"Click Chemistry and Applications","score":0.07840000092983246,"subfield":{"id":"https://openalex.org/subfields/1605","display_name":"Organic Chemistry"},"field":{"id":"https://openalex.org/fields/16","display_name":"Chemistry"},"domain":{"id":"https://openalex.org/domains/3","display_name":"Physical Sciences"}},{"id":"https://openalex.org/T12893","display_name":"Organic Chemistry Cycloaddition Reactions","score":0.033900000154972076,"subfield":{"id":"https://openalex.org/subfields/1605","display_name":"Organic Chemistry"},"field":{"id":"https://openalex.org/fields/16","display_name":"Chemistry"},"domain":{"id":"https://openalex.org/domains/3","display_name":"Physical Sciences"}}],"keywords":[{"id":"https://openalex.org/keywords/benzyne","display_name":"benzyne","score":0.7850000262260437},{"id":"https://openalex.org/keywords/click-chemistry","display_name":"click chemistry","score":0.6480000019073486},{"id":"https://openalex.org/keywords/3-2-cycloaddition","display_name":"[3+2] cycloaddition","score":0.8880000114440918},{"id":"https://openalex.org/keywords/azide-alkyne-cycloaddition","display_name":"azide-alkyne cycloaddition","score":0.8859999775886536},{"id":"https://openalex.org/keywords/photoinitiated-reactions","display_name":"photoinitiated reactions","score":0.824999988079071},{"id":"https://openalex.org/keywords/azide","display_name":"azide","score":0.5590000152587891},{"id":"https://openalex.org/keywords/alkynes","display_name":"alkynes","score":0.8550000190734863},{"id":"https://openalex.org/keywords/functional-group-tolerance","display_name":"functional group tolerance","score":0.6970000267028809},{"id":"https://openalex.org/keywords/polar-protic-solvents","display_name":"polar protic solvents","score":0.7820000052452087}],"concepts":[{"id":"https://openalex.org/C171811041","wikidata":"https://www.wikidata.org/wiki/Q416633","display_name":"Aryne","level":2,"score":0.9867099523544312},{"id":"https://openalex.org/C2779664164","wikidata":"https://www.wikidata.org/wiki/Q898648","display_name":"Cycloaddition","level":3,"score":0.9548479318618774},{"id":"https://openalex.org/C185592680","wikidata":"https://www.wikidata.org/wiki/Q2329","display_name":"Chemistry","level":0,"score":0.8223500847816467},{"id":"https://openalex.org/C69610077","wikidata":"https://www.wikidata.org/wiki/Q912270","display_name":"Click chemistry","level":2,"score":0.6100966334342957},{"id":"https://openalex.org/C2780997848","wikidata":"https://www.wikidata.org/wiki/Q407627","display_name":"Azide","level":2,"score":0.5056467056274414},{"id":"https://openalex.org/C21951064","wikidata":"https://www.wikidata.org/wiki/Q899212","display_name":"Combinatorial chemistry","level":1,"score":0.48277512192726135},{"id":"https://openalex.org/C75473681","wikidata":"https://www.wikidata.org/wiki/Q188651","display_name":"Photochemistry","level":1,"score":0.4634295403957367},{"id":"https://openalex.org/C2778012447","wikidata":"https://www.wikidata.org/wiki/Q1034415","display_name":"Scope (computer science)","level":2,"score":0.43081533908843994},{"id":"https://openalex.org/C147597530","wikidata":"https://www.wikidata.org/wiki/Q369472","display_name":"Computational chemistry","level":1,"score":0.358889639377594},{"id":"https://openalex.org/C178790620","wikidata":"https://www.wikidata.org/wiki/Q11351","display_name":"Organic chemistry","level":1,"score":0.29855069518089294},{"id":"https://openalex.org/C161790260","wikidata":"https://www.wikidata.org/wiki/Q82264","display_name":"Catalysis","level":2,"score":0.13757294416427612},{"id":"https://openalex.org/C41008148","wikidata":"https://www.wikidata.org/wiki/Q21198","display_name":"Computer science","level":0,"score":0.08038532733917236},{"id":"https://openalex.org/C199360897","wikidata":"https://www.wikidata.org/wiki/Q9143","display_name":"Programming language","level":1,"score":0.057306379079818726}],"mesh":[],"locations_count":2,"locations":[{"id":"doi:10.1021/ol500389t","doi":"https://doi.org/10.1021/ol500389t","is_oa":false,"landing_page_url":"https://doi.org/10.1021/ol500389t","pdf_url":null,"source":{"id":"https://openalex.org/S201989124","display_name":"Organic Letters","issn_l":"1523-7052","issn":["1523-7052","1523-7060"],"is_oa":false,"is_in_doaj":false,"is_core":true,"listed_in":["cwts-core","dongbi-a","jufo-2","ki-jl-2","medline","norway-2","poland-140","russia-white-list-1","vabb-shw"],"host_organization":"https://openalex.org/P4310320006","host_organization_name":"American Chemical Society","host_organization_lineage":["https://openalex.org/P4310320006"],"host_organization_lineage_names":["American Chemical Society"],"type":"journal"},"license":null,"license_id":null,"version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"Organic Letters","raw_type":"journal-article"},{"id":"pmid:24625300","doi":null,"is_oa":false,"landing_page_url":"https://pubmed.ncbi.nlm.nih.gov/24625300","pdf_url":null,"source":{"id":"https://openalex.org/S4306525036","display_name":"PubMed","issn_l":null,"issn":null,"is_oa":false,"is_in_doaj":false,"is_core":false,"listed_in":[],"host_organization":"https://openalex.org/I1299303238","host_organization_name":"National Institutes of Health","host_organization_lineage":["https://openalex.org/I1299303238"],"host_organization_lineage_names":[],"type":"repository"},"license":null,"license_id":null,"version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"Organic letters","raw_type":"Journal Article"}],"best_oa_location":null,"sustainable_development_goals":[],"study_designs":[],"awards":[],"funders":[],"has_content":{"pdf":false,"grobid_xml":false},"content_urls":null,"referenced_works_count":26,"referenced_works":["https://openalex.org/W1968222033","https://openalex.org/W1974716562","https://openalex.org/W1985200262","https://openalex.org/W1987334051","https://openalex.org/W2007736465","https://openalex.org/W2020210562","https://openalex.org/W2021946498","https://openalex.org/W2029389567","https://openalex.org/W2030412163","https://openalex.org/W2033945317","https://openalex.org/W2039730742","https://openalex.org/W2051045615","https://openalex.org/W2057315451","https://openalex.org/W2057916037","https://openalex.org/W2077790287","https://openalex.org/W2085002507","https://openalex.org/W2087171377","https://openalex.org/W2090406639","https://openalex.org/W2103913936","https://openalex.org/W2131188581","https://openalex.org/W2132716817","https://openalex.org/W2137577190","https://openalex.org/W2141268937","https://openalex.org/W2149849271","https://openalex.org/W2321864641","https://openalex.org/W4256503849"],"related_works":["https://openalex.org/W2949470936","https://openalex.org/W2055212679","https://openalex.org/W2953329764","https://openalex.org/W7095331173","https://openalex.org/W1985200262","https://openalex.org/W2321914836","https://openalex.org/W2077183018","https://openalex.org/W2978616834","https://openalex.org/W4414660506","https://openalex.org/W2040909405"],"abstract_inverted_index":{"The":[0,51],"[3":[1,32],"+":[2,33],"2]":[3,34],"cycloaddition":[4,35,98],"of":[5,39,42,64,88,96],"azides":[6],"and":[7,19,67,86],"alkynes":[8],"has":[9],"proven":[10],"invaluable":[11],"across":[12],"numerous":[13],"scientific":[14],"disciplines":[15],"for":[16,73],"imaging,":[17],"cross-linking,":[18],"site-specific":[20],"labeling":[21],"among":[22],"many":[23],"other":[24],"applications.":[25],"We":[26],"have":[27],"developed":[28],"a":[29,40,61],"photoinitiated,":[30],"benzyne-based":[31],"that":[36],"is":[37,53,71],"tolerant":[38],"variety":[41],"functional":[43],"groups":[44],"as":[45,47,92,94],"well":[46,93],"polar,":[48],"protic":[49],"solvents.":[50],"reaction":[52,91],"complete":[54],"on":[55],"the":[56,68,84,89,97],"minute":[57],"time":[58],"scale":[59],"using":[60],"single":[62],"equivalent":[63],"partner":[65],"azide,":[66],"benzyne":[69],"photoprecursor":[70],"stable":[72],"months":[74],"under":[75],"ambient":[76],"light":[77],"at":[78],"room":[79],"tempurature.":[80],"Herein":[81],"we":[82],"report":[83],"optimization":[85],"scope":[87],"photoinitiated":[90],"characterization":[95],"products.":[99]},"counts_by_year":[{"year":2026,"cited_by_count":4},{"year":2025,"cited_by_count":5},{"year":2024,"cited_by_count":4},{"year":2023,"cited_by_count":4},{"year":2022,"cited_by_count":4},{"year":2021,"cited_by_count":10},{"year":2020,"cited_by_count":3},{"year":2019,"cited_by_count":6},{"year":2018,"cited_by_count":3},{"year":2017,"cited_by_count":5},{"year":2016,"cited_by_count":2},{"year":2015,"cited_by_count":8},{"year":2014,"cited_by_count":3},{"year":2013,"cited_by_count":1}],"updated_date":"2026-10-12T09:40:04.860316","created_date":"2016-06-24T00:00:00"}